The Experiment of Suzuki Coupling of 4-bromoacetophenone (S)

Shauna Foreman
Courtney Hermany

Limiting Reagent:

4-bromoacetophenone phenylboronic acid potassium carbonate phase transfer catalyst 4-acetylbiphenyl

palladium acetate catalyst

4 bromoacetophenone:
0.198 g 4 bromoacetophenone x 1 mol 4 bromoacetophenone= 0.000995 mols 4 bromoacetophenone
199.04 g 4 bromoacetophenone

phenylboronic acid:
0.137g phenylboronic acid x 1 mol phenylboronic acid = 0.001124 mols phenylboronic acid
121.93 g phenylboronic acid

potassium carbonate:
0.35 g potassium carbonate x 1 mol potassium carbonate = 0.00253 mols potassium carbonate
138.205 g potassium carbonate

Experimentally Recovered Product Mass: 0.112 g 4-acetylbiphenyl

Theoretical Product Mass:

0.000995 mol 4 bromoacetophenone x 1 mol 4-acetylbiphenyl x 196.24 g 4-acetylbiphenyl = 0.195 g 4-acetylbiphenyl

1 mol 4 bromoacetophenone 1 mol 4-acetylbiphenyl

% Yield:
0.112 g4-acetylbiphenyl x 100= 57.44%
0.195 g 4-acetylbiphenyl

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 Experimental data for benzoic acid product:

Exactly 0.198 g of 4 bromoacetophenone, 0.137 g of phenylboronic acid, 0.0020

g of palladium acetate, 0.321 g of tetrabutyl ammonium, and 0.35 g of potassium
carbonate was added to a 5mL round bottom flask. Exactly 1 mL of H 20 was then
added to the round bottom flask and the catalyst. This was then added to a sand
bath and a spin vane was added with a stir rate of 5. The product was dark in
color and at the end of 45 minutes the temperature reached 115°C. The dark
grey solid was formed and was ready for filtrate. Exactly 10mL of hot water was
added to the filtrate After the solid was left behind exactly 3 mL of acetone was
added, then put in the centrifuge for two minutes. Exactly 3 drops of H 20 was
added to the remaining solid after the brown liquid was decanted, then added to
an ice bath. The remaining product mass was 0.112 g and the final product was
4-acetylbiphenyl.

MP: (C°)(116-118°C literature), (116.5-117.3°C experimental)

IR(ATR) cm-1 : N/A

Error Analysis by number: 1,2,3,4,5a,5b,6a,6b,6e

Commercial Use for biphenyl Products: Biphenyl products can be used in textile
dyes and in food preservation, controlling the fungi in not allowing it to grow.

This study source was downloaded by 100000820116497 from CourseHero.com on 07-10-2023 12:09:47 GMT -05:00

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